First of all, this is the 50th Anniversary of the show, so that is reason enough to attend. I've been going there almost since it opened, but have missed the last few years due to a broken leg, etc. So, I've seen it change over the years. Always a great show with the latest and greatest boats to visit and lots of sailing gear in tents and reps, builders and professional people to talk to about whatever you want to talk about sailing. There are charter companies so you can get a handle on that and maybe even book a charter. Lots of places to eat in Annapolis (and drink). Seafood is wonderful, the Maryland Crab is plentiful and fun to eat at a place like Mike's or Cantler's). Great pubs and food places like McGarvy's, Middleton Tavern (oyster shooters), O'Leary's (seafood), Chart House (food and drink in a super nice setting over the harbor), Ruth Chris or Lewne's if you are into red meat, Davie's Pub for a cool sailor bar off the beaten track, and the list goes on. I've never met up with SBO peeps. Wouldn't recognize you if I did, I guess. But, it is definitely worth seeing, but better book because rooms get hard to find. The longer you wait, the further out you have to go to find a room (Glen Burnie). And side trips are always inviting. The Naval Academy with a great maritime museum and the cript of John Paul Jones, St. Michaels museum across the Bay and south. Kent Island. Baltimore harbor. Little Italy in Baltimore. Fells Point restaurants in Baltimore. You can drive the loop and go across the Bay Bridge, and head south on the Eastern Shore to St. Michaels and then Easton and Oxford and then catch a ferry back to the other side and work your way back up to Annapolis. Peeps have only so much time to take side trips it seems, but there are lots of things to do around Annapolis and nearby. Walk up the hills to other restaurants and shops galore. Helly Hansen has a store with usually great clothing discounts during the show. I could almost write a book about it. There are two West Marine stores in Annapolis too, plus Fawcett's store and a others. Bacon and Associates (used sails and equipment) on Legion Avenue off of West Street is a great place to browse and if you are looking for any used sails, that is one of the best places to go. Their inventory is anything from Optimist dinghies to Whitbread boats. They are closed on Sunday though. And, of course, new sails are on display at the show with show discounts. Like beer? Yuengling is America's oldest brewery and you can fine that fine brew in abundance in Annapolis. Need I say more?